Skip to main content
SpringerLink
Log in

CTAB–tributylstannic[3-(3′,4′-dichlorophenylamido)propanoate] interaction: a tool for predicting organotin(IV) complex–cell membrane interaction parameters

  • Original Contribution
  • Published:
Colloid and Polymer Science Aims and scope Submit manuscript

Abstract

This study attempts to explain the bioavailability, permeability, and interaction parameters of organotin(IV) derivatives with the cell membrane. For this purpose, tributylstannic[3-(3′,4′-dichlorophenylamido)propanoate] was synthesized and characterized by elemental analysis and spectroscopic methods (Fourier transform infrared spectroscopy (FT-IR), 1H, 13C, 119Sn NMR). The organic anion was found to act as monodentate O-bound ligand in solution. Cationic surfactant cetyl N,N,N-trimethylammoniumbromide (CTAB) was used to study the interactions of the organotin(IV) complex with positively charged molecules of the surfactant acting as a model cell membrane. The thermodynamic parameters of complex–CTAB interaction concluded that the complex is located in the peripheral region of CTAB micelles. The redshifts in the UV spectra of the complex confirmed its solubilization into micelles. The two carbonyl oxygen atoms were found to be binding sites of the complex with CTAB.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Scheme 1
Fig. 1
Scheme 2
Fig. 2
Fig. 3
Fig. 4

Similar content being viewed by others

References

  1. Tabassum S, Pettinari C (2006) Chemical and biotechnological developments in organotin cancer chemotherapy. J Organomet Chem 691(8):1761–1766. doi:10.1016/j.jorganchem.2005.12.033

    Article  CAS  Google Scholar 

  2. Gielen M, Biesemans M, Willem R (2005) Organotin compounds: from kinetics to stereochemistry and antitumour activities. Appl Organomet Chem 19(4):440–450. doi:10.1002/aoc.771

    Article  CAS  Google Scholar 

  3. Ashfaq M, Khan MI, Baloch MK, Malik A (2004) Biologically potent organotin(IV) complexes of 2-maleimidoacetic acid. J Organomet Chem 689(1):238–245. doi:10.1016/j.jorganchem.2003.10.007

    Article  CAS  Google Scholar 

  4. Kaluđerović GN, Paschke R, Prashar S, Gómez-Ruiz S (2010) Synthesis, characterization and biological studies of 1-D polymeric triphenyltin(IV) carboxylates. J Organomet Chem 695(15–16):1883–1890. doi:10.1016/j.jorganchem.2010.04.029

    Google Scholar 

  5. Khan MI, Kaleem Baloch M, Ashfaq M (2004) Biological aspects of new organotin(IV) compounds of 3-maleimidopropionic acid. J Organomet Chem 689(21):3370–3378. doi:10.1016/j.jorganchem.2004.07.049

    Article  CAS  Google Scholar 

  6. Chicano JJ, Ortiz A, Teruel JA, Aranda FJ (2001) Organotin compounds alter the physical organization of phosphatidylcholine membranes. Biochim Biophys Acta 1510(1–2):330–341. doi:10.1016/S0005-2736(00)00365-5

    Article  CAS  Google Scholar 

  7. Kim DH, Lee SK, Kim WS, Yang JS, Lee DW (2001) Quantitative retention activity relationship of quinolones using micellar liquid chromatography. J Liq Chromatogr Relat Technol 24(9):1309–1322. doi:10.1081/JLC-100103449

    Article  CAS  Google Scholar 

  8. Shah FA, Fatima K, Sabir S, Ali S, Qadri I (2014) Tributyltin(IV)[3-(3′,5′-dimethylphenylamido)propanoate] as a potent HCV inhibitor, its delivery study, controlled release and binding sites using CTAB as a standard cell membrane. Appl Organomet Chem 28(2):74–80. doi:10.1002/aoc.3079

    Article  CAS  Google Scholar 

  9. Armarego WL, Chai CLL (2013) Purification of laboratory chemicals. Butterworth-Heinemann

  10. Shah FA, Tahir MN, Ali S, Ahmed S, Danish M (2009) 3-[(3,4-Dichlorophenyl)aminocarbonyl]propionic acid. Acta Crystallogr Sect E 65(5):o1130. doi:10.1107/S1600536809015025

    Article  CAS  Google Scholar 

  11. Rehman W, Baloch MK, Badshah A (2005) Comparative study of structure: activity relationship of di and triorganotin (IV) complexes of monomethyl glutarate. J Braz Chem Soc 16:827–834

    Article  CAS  Google Scholar 

  12. Mahmood S, Ali S, Bhatti M, Shahid K, Shahzadi S, Mazhar M, Khan K, Maharvi G (2004) Synthetic, spectroscopic, thermal and biological studies of tri-, di-and chlorodiorganotin (IV) 2-(4-isobutylphenyl) propanoate. J Chem Soc Pak 26(1):61–68

    CAS  Google Scholar 

  13. Tariq M, Muhammad N, Sirajuddin M, Ali S, Shah NA, Khalid N, Tahir MN, Khan MR (2013) Synthesis, spectroscopic characterization, X-ray structures, biological screenings, DNA interaction study and catalytic activity of organotin(IV) 3-(4-flourophenyl)-2-methylacrylic acid derivatives. J Organomet Chem 723:79–89. doi:10.1016/j.jorganchem.2012.09.011

    Article  CAS  Google Scholar 

  14. Dakternieks D, Duthie A, Smyth DR, Stapleton CPD, Tiekink ERT (2003) Steric control over molecular structure and supramolecular association exerted by tin- and ligand-bound groups in diorganotin carboxylates. Organometallics 22 (22):4599–4603. doi:10.1021/om0340140

  15. Willem R, Verbruggen I, Gielen M, Biesemans M, Mahieu B, Basu Baul TS, Tiekink ERT (1998) Correlating Mössbauer and solution- and solid-state 117Sn NMR data with X-ray diffraction structural data of triorganotin 2-[(E)-2-(2-hydroxy-5-methylphenyl)-1-diazenyl]benzoates. Organometallics 17(26):5758–5766. doi:10.1021/om980504u

    Article  CAS  Google Scholar 

  16. Liu T-Q, Guo R (2006) Influence of low cetyltrimethylammonium bromide concentration on the interactions and properties of hemoglobin with acyclovir. Chin J Chem 24(5):620–626. doi:10.1002/cjoc.200690119

    Article  CAS  Google Scholar 

  17. Shah SS, Saeed A, Sharif QM (1999) A study of micellization parameters and electrostatic interactions in micellar solution of sodium dodecyl sulfate. Colloids Surf Physicochem Eng Aspects 155(2–3):405–412. doi:10.1016/S0927-7757(99)00021-7

    Article  CAS  Google Scholar 

  18. Farías T, de Ménorval LC, Zajac J, Rivera A (2009) Solubilization of drugs by cationic surfactants micelles: conductivity and 1H NMR experiments. Colloids Surf Physicochem Eng Aspects 345(1–3):51–57. doi:10.1016/j.colsurfa.2009.04.022

    Article  Google Scholar 

  19. Shah SS, Ali Awan M, Ashraf M, Idris SA (1995) Solubilization of phenol and benzyl alcohol by cationic and anionic surfactant micelles. Colloids Surf Physicochem Eng Aspects 105(2–3):319–323. doi:10.1016/0927-7757(95)03335-1

    Article  CAS  Google Scholar 

  20. Shah SS, Khan MS, Ullah H, Awan MA (1997) Solubilization of amphiphilic hemicyanine dyes by a cationic surfactant, cetyltrimethylammonium bromide. J Colloid Interface Sci 186(2):382–386. doi:10.1006/jcis.1996.4649

    Article  CAS  Google Scholar 

  21. Kawamura H, Manabe M, Miyamoto Y, Fujita Y, Tokunaga S (1989) Partition coefficients of homologous.omega.-phenylalkanols between water and sodium dodecyl sulfate micelles. J Phys Chem 93 (14):5536–5540. doi:10.1021/j100351a042

  22. Valero M, Del Arco-Gómez A, Rodríguez L (2002) New insight into the structure of CTAB micelles in the presence of cyclodextrins, using non-steroidic anti-inflammatory agents – nabumetone, naproxen—as fluorescent probes. J Incl Phenom Macrocycl Chem 42(1–2):121–130. doi:10.1023/A:1014521623774

    Article  CAS  Google Scholar 

  23. Park JW, Lee SY, Kim SM (2005) Efficient inclusion complexation and intra-complex excitation energy transfer between aromatic group-modified β-cyclodextrins and a hemicyanine dye. J Photochem Photobiol A: Chem 173(3):271–278. doi:10.1016/j.jphotochem.2005.04.006

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Department of Chemistry, Quaid-i-Azam University, Islamabad, 45320, Pakistan

    Farooq Ali Shah & Saqib Ali

  2. Department of Chemistry, COMSATS Institute of Information Technology, Abbottabad, KPK, 22060, Pakistan

    Asad Muhammad Khan

  3. Research Complex, Department of chemistry, Allama Iqbal Open University, Islamabad, Pakistan

    Shaista Sabir

Authors
  1. Farooq Ali Shah
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Asad Muhammad Khan
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Shaista Sabir
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Saqib Ali
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Saqib Ali.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Shah, F.A., Khan, A.M., Sabir, S. et al. CTAB–tributylstannic[3-(3′,4′-dichlorophenylamido)propanoate] interaction: a tool for predicting organotin(IV) complex–cell membrane interaction parameters. Colloid Polym Sci 294, 87–94 (2016). https://doi.org/10.1007/s00396-015-3738-x

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s00396-015-3738-x

Keywords

Search

Navigation